The long term objective of this proposal is to determine how fungal secondary metabolism is controlled and to identify the biological role(s) this enigmatic process plays in the producing organism. Fungal secondary metabolism, although seldom the object of fashionable basic research, is critically important to society as a source of beneficial drugs, and toxins that affect man and animals. Specifically, we will focus on a set of six structurally-related dioxopiperazines produced by Penicillium brevicompactum--the brevianamides A through F. Preliminary results suggest that brevianamide production correlates with conidiation in this organism. During the three years of the project we hope to establish: how the 2,2,2-diazabicyclooctane and psi-indoxyl moieties of brevianamides A-D are formed; the extent and mechanism of brevianamide turn-over; and the type(s) of cell(s) in the culture that is/are responsible for biosynthesis/turnover. These are all intriguing questions in their own right; they also will provide the necessary informational basis from which an attack on the problems of control and function of brevianamide production, can be launched. As a minor component of the project we will determine if the production of structurally analogous prenylated dioxopiperazines--the austamides of Aspergillus ustus, echinulin in A. amstelodami and verruculugen in P. verruculosum also correlates with the process of conidiation.